On November 6 2009, I mailed a petition for legal name change, along with a certified copy of my birth certificate and the $185 fee (in MA). Luckily, my father mailed me my birth certificate in 2006 so I didn't have to deal with people in Illinois over the phone and pay $20 or whatever for a copy. And because I wasn't changing my last name, I didn't have to publish it in any local news papers.
On December 14 2009, a judge approved it in just a couple minutes! I was a bit disappointed with how anti-climactic it was, considering I'd been wanting to get it done since 2004.
On January 7 2010, I went with a friend to their legal name change so we could both get new social security cards. Fortunately, there's no fee for that! I got my new card on the 15th of that month.
On February 16 2010, I finally went to the RMV to get a new Massachusetts ID. It cost $25. Around that time, the RMV had gotten trans training and changed their policy on changing gender markers, so I wasn't expecting any sort of hassle. I went up to the counter with my court paperwork and told him that I just needed to change the name on my ID. He pointed to the gender marker on my card with my birth name and asked, "What about this? Do you want to change this too?" In Massachusetts, a letter from a therapist or doctor is required for that to be changed, and since I didn't have said letter, I told him that I couldn't change my marker at this time - just the name, please. He continued to make a fuss, but eventually he issued my temporary ID (I decided not to take a new picture since I'd had one on file that was only months old) and I was told I'd get my real one in about two weeks.
On February 22 2010, I got my ID in the mail!
On May 28 2010, all of my utilities were changed to reflect my name change (some places are more of a pain in the ass to do that than others), and I randomly got a new insurance card without applying for it (I assume it had something to do with getting my social security card).
On May 20 2014, I finally went back to the RMV to change the picture and gender marker on my ID. I could have done this after coming home after top surgery, but I decided to wait until my ID expired on my 27th birthday since nobody ever paid attention to the gender marker anyway. And, procrastinator that I am, held off for another five months!
On June 9 2014, I went to the social security office to change my gender marker in my records. My state insurance had suddenly started noticing the month or so before that my gender marker wasn't accurate, and it seemed as good a time as any to get it done anyway since Medicare - insurance that I get through social security disability - lifted its ban on covering trans-specific treatment. I needed to get Testopel fully covered (which insurance couldn't do while my gender marker was F... because reasons, I guess) because even the co-pay would have been beyond my means. The person at the social security office told me that the change in my records would take 24 hours, but I still wound up arguing for about a week with the pharmacy filling my Testopel order. More on that here.
To date, I've yet to change the name and gender marker on my birth certificate. I decided to wait until after I had a hysterectomy, to avoid sending up any sort of red flags, but it's not currently pressing.